5-Chloro-2,3-Diphenylpyrazine → 4-((5,6-Diphenyl-Pyrazin-2-yl)(isopropyl)amino)butan-1-ol

HRID 1271273Notes

Reaction equation

HRID 1271273 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[CH:20]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])([CH3:22])[CH3:21]>O>[C:8]1([C:5]2[N:6]=[CH:7][C:2]([N:23]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:20]([CH3:22])[CH3:21])=[N:3][C:4]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 36544935-Chloro-2,3-DiphenylpyrazineHCID 129509864-(Isopropylamino)butanol

Product 1

HCID 184526554-((5,6-Diphenyl-Pyrazin-2-yl)(isopropyl)amino)butan-1-olYield 56.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

30 g of 2-chloro-5,6-diphenylpyrazine and 131.22 g of 4-(isopropylamino)-1-butanol were mixed and then heated with stirring at 190° C. for 10 hours. The reaction solution was air-cooled, poured into water, extracted with diethyl ether, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography to obtain 22.96 g of the desired compound as a colorless crystal having a melting point of 102 to 103° C.

Workup

  1. temperatureheated
  2. temperatureThe reaction solution was air-cooled
  3. extractionextracted with diethyl ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-890b16c371fd48258757dc6e2322cad6
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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